Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

[Image: see text] In this contribution, we report chemoenzymatic bromodecarboxylation (Hunsdiecker-type) of α,ß-unsaturated carboxylic acids. The extraordinarily robust chloroperoxidase from Curvularia inaequalis (CiVCPO) generated hypobromite from H(2)O(2) and bromide, which then spontaneously reac...

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Autores principales: Li, Huanhuan, Younes, Sabry H. H., Chen, Shaohang, Duan, Peigao, Cui, Chengsen, Wever, Ron, Zhang, Wuyuan, Hollmann, Frank
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9016706/
https://www.ncbi.nlm.nih.gov/pubmed/35465241
http://dx.doi.org/10.1021/acscatal.2c00485
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author Li, Huanhuan
Younes, Sabry H. H.
Chen, Shaohang
Duan, Peigao
Cui, Chengsen
Wever, Ron
Zhang, Wuyuan
Hollmann, Frank
author_facet Li, Huanhuan
Younes, Sabry H. H.
Chen, Shaohang
Duan, Peigao
Cui, Chengsen
Wever, Ron
Zhang, Wuyuan
Hollmann, Frank
author_sort Li, Huanhuan
collection PubMed
description [Image: see text] In this contribution, we report chemoenzymatic bromodecarboxylation (Hunsdiecker-type) of α,ß-unsaturated carboxylic acids. The extraordinarily robust chloroperoxidase from Curvularia inaequalis (CiVCPO) generated hypobromite from H(2)O(2) and bromide, which then spontaneously reacted with a broad range of unsaturated carboxylic acids and yielded the corresponding vinyl bromide products. Selectivity issues arising from the (here undesired) addition of water to the intermediate bromonium ion could be solved by reaction medium engineering. The vinyl bromides so obtained could be used as starting materials for a range of cross-coupling and pericyclic reactions.
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spelling pubmed-90167062022-04-20 Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids Li, Huanhuan Younes, Sabry H. H. Chen, Shaohang Duan, Peigao Cui, Chengsen Wever, Ron Zhang, Wuyuan Hollmann, Frank ACS Catal [Image: see text] In this contribution, we report chemoenzymatic bromodecarboxylation (Hunsdiecker-type) of α,ß-unsaturated carboxylic acids. The extraordinarily robust chloroperoxidase from Curvularia inaequalis (CiVCPO) generated hypobromite from H(2)O(2) and bromide, which then spontaneously reacted with a broad range of unsaturated carboxylic acids and yielded the corresponding vinyl bromide products. Selectivity issues arising from the (here undesired) addition of water to the intermediate bromonium ion could be solved by reaction medium engineering. The vinyl bromides so obtained could be used as starting materials for a range of cross-coupling and pericyclic reactions. American Chemical Society 2022-04-04 2022-04-15 /pmc/articles/PMC9016706/ /pubmed/35465241 http://dx.doi.org/10.1021/acscatal.2c00485 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Li, Huanhuan
Younes, Sabry H. H.
Chen, Shaohang
Duan, Peigao
Cui, Chengsen
Wever, Ron
Zhang, Wuyuan
Hollmann, Frank
Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids
title Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids
title_full Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids
title_fullStr Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids
title_full_unstemmed Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids
title_short Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids
title_sort chemoenzymatic hunsdiecker-type decarboxylative bromination of cinnamic acids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9016706/
https://www.ncbi.nlm.nih.gov/pubmed/35465241
http://dx.doi.org/10.1021/acscatal.2c00485
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